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Association behavior of porphyrin pendants in pH-sensitive water-soluble polymer

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Abstract

A novel tripyridylporphyrin monomer, 5-[4-[2-(acryloyloxy)ethoxy]phenyl]-l0,l5,20-tris(4-pyridyl)porphyrin (TrPyP), was synthesized and polymerized with acrylamide (AM) to prepare the hydrophobically associating water-soluble polymer PAM-TrPyP. The aggregation behavior of porphyrin pendants was investigated by UV-Visible and fluorescence spectra. The polymer displays a strong tendency of hydrophobic association even in dilute solutions. With increasing the concentration, the maximum absorption wavelength of Soret band changes from 416 nm to 407 nm, and the fluorescence corrected for the inner filter effect exhibits moderate concentration quenching. All the results indicate that π-π interaction of porphyrin pendants plays a key role in association of PAM-TrPyP, and H-aggregates of porphyrins are mainly formed in the concentrated solution. On the other hand, dynamic light scattering (DLS) and transmission electron microscopy (TEM) were used to follow the changes in size and structure of the macromolecular assemblies with the concentration increase. The polymer aggregation conformation changes from loose “vesicle-like” morphology to solid globule accordingly. When pH value of solution decreases to 4.3, pyridine moieties on porphyrin pendants could be protonated and the H-aggregates formed in macromolecular matrix are destroyed by electrostatic repulsion interactions.

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References

  1. Beletskaya, I., Tyurin, V.S., Tsivadze, A.Y., Guilard, R. and Stern, C., Chem. Rev., 2009, 109: 1659

    Article  CAS  Google Scholar 

  2. Satake, A. and Kobuke, Y., Tetrahedron, 2005, 61: 13

    Article  CAS  Google Scholar 

  3. Choi, M.S., Tetrahedron Lett., 2008, 49: 7050

    Article  CAS  Google Scholar 

  4. Tait, M.J. and Franks, F., Nature, 1971, 230: 91

    Article  CAS  Google Scholar 

  5. Gandini, S.C.M., Yushmanov, V.E., Borissevitch, I.E. and Tabak, M., Langmuir, 1999, 15: 6233

    Article  CAS  Google Scholar 

  6. Scolaro, L.M., Donato, C., Castriciano, M., Romeo, A. and Romeo, R., Inorg. Chim. Acta, 2000, 300–302: 978

    Article  Google Scholar 

  7. Iida, K., Nango, M., Matsuura, M., Yamaguchi, M., Sato, K., Tanaka, K., Akimoto, K., Yamashita, K., Tsuda, K. and Kurono Y., Langmuir, 1996, 12: 450

    Article  Google Scholar 

  8. Li, J.B., An, Y.L., Chen, X., Xiong, D.A., Li, Y., Huang, N. and Shi, L.Q., Macromol. Rapid Commun, 2008, 29: 214

    Article  CAS  Google Scholar 

  9. Morishima, Y., Chinese J. Polym. Sci., 2000, 18(4): 323

    CAS  Google Scholar 

  10. Nowakowska, M., Karewicz, A., Loukine, N. and Guillet, J.E., Polymer, 2002, 43: 2003

    Article  CAS  Google Scholar 

  11. Kamachi, M., Cheng, X.S., Kida, T., Kajiwara, A., Shibasaka, M. and Nagata, S., Macromolecules, 1987, 20: 2665

    Article  CAS  Google Scholar 

  12. Nowakowska, M., Karewicz, A., Kłos, M. and Zapotoczny, S., Macromolecules, 2003, 36: 4134

    Article  CAS  Google Scholar 

  13. Wang, R.M., He, Y.F., Lei, Z.Q., Wang, Y.P. and Li, S.B., Chinese J. Polym. Sci., 1998, 16(1): 91

    CAS  Google Scholar 

  14. Zhou, Q.F., Zhu, X.L. and Wen, Z.Q., Macromolecules, 1989, 22: 491

    Article  CAS  Google Scholar 

  15. Malik, S., Kawano, S.-I., Fujita, N. and Shinkai, S., Tetrahedron, 2007, 63: 7326

    Article  CAS  Google Scholar 

  16. Casas, C., Saint-Jalmes, B., Loup, C., Lacey, C.J. and Meunier, B., J. Org. Chem., 1993, 58: 2913

    Article  CAS  Google Scholar 

  17. Kasha, M., Rawls, H.R. and El-Bayoumi, M.A., Pure Appl. Chem., 1965, 11: 371

    Article  CAS  Google Scholar 

  18. Andrade, S.M., Teixeira, C., Togashi, D.M., Costa, S.M.B. and Sobral, A.J.F.N., J. Photochem. Photobiol., A, 2006, 178: 225

    Article  CAS  Google Scholar 

  19. Stella, L., Capodilupo, A.L. and Bietti, M., Chem. Commun., 2008, (39): 4744

  20. Zozulya, V.N., Ryazanova, O.A., Voloshin, I.M., Glamazda, A.Y. and Karachevtsev, V.A., J. Fluoresc., 2010, 20: 695

    Article  CAS  Google Scholar 

  21. Thyagarajan, S., Leiding, T., Årsköld, S.P., Cheprakov, A.V. and Vinogradov, S.A., Inorg. Chem., 2010, 49: 9909

    Article  CAS  Google Scholar 

  22. Yue, B.H., Huang, C.-Y., Nieh, M.-P., Glinka, C.J. and Katsaras, J., J. Phys. Chem. B, 2005, 109: 609

    Article  CAS  Google Scholar 

  23. Kim, S.Y., Lee, K.E., Han, S.S. and Jeong, B., J. Phys. Chem. B, 2008, 112: 7420

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing, 100190, China

    Ke-wei Ding, Fei Wang & Fei-peng Wu  (吴飞鹏)

  2. Graduate University of Chinese Academy of Sciences, Beijing, 100049, China

    Ke-wei Ding & Fei Wang

Authors
  1. Ke-wei Ding
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  2. Fei Wang
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  3. Fei-peng Wu  (吴飞鹏)
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Correspondence to Fei-peng Wu  (吴飞鹏).

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Ding, Kw., Wang, F. & Wu, Fp. Association behavior of porphyrin pendants in pH-sensitive water-soluble polymer. Chin J Polym Sci 30, 63–71 (2012). https://doi.org/10.1007/s10118-012-1104-8

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  • DOI: https://doi.org/10.1007/s10118-012-1104-8

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